6-Methyl-4-oxo-4H-chromene-3-carbaldehyde.

In the title compound, C(11)H(8)O(3), the benzopyran-4-one or chromone ring system is almost planar, with a maximum deviation of 0.045 (2) Å. The crystal structure is stablized by π-π inter-actions between the benzene and pyran rings of inversion-related mol-ecules stacked along the b axis, with a centroid-centroid distance of 3.5463 (12) Å

Related literature

For the biological activity of chromone, see: Patel et al. (2011 ▶); Khan et al. (2009 ▶, 2010 ▶); Gautam et al. (2010 ▶); Ishar et al. (2006 ▶); Hassan (1992 ▶); Nohara et al. (1974 ▶). For a related structure, see: Wang & Kong (2007 ▶).

Experimental

Crystal data

C11H8O3

M = 188.17

Triclinic,

a = 6.6945 (7) Å

b = 7.1079 (7) Å

c = 10.3032 (11) Å

α = 71.593 (2)°

β = 84.962 (2)°

γ = 69.843 (2)°

V = 436.57 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 273 K

0.26 × 0.23 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.973, T max = 0.989

4974 measured reflections

1629 independent reflections

1300 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.152

S = 1.07

1629 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037555/rz2798sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037555/rz2798Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037555/rz2798Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H8O3	Z = 2
Mr = 188.17	F(000) = 196
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6945 (7) Å	Cell parameters from 1636 reflections
b = 7.1079 (7) Å	θ = 3.2–28.1°
c = 10.3032 (11) Å	µ = 0.11 mm−1
α = 71.593 (2)°	T = 273 K
β = 84.962 (2)°	Block, colorles
γ = 69.843 (2)°	0.26 × 0.23 × 0.11 mm
V = 436.57 (8) Å3

Bruker SMART APEX CCD area-detector diffractometer	1629 independent reflections
Radiation source: fine-focus sealed tube	1300 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω scan	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.973, Tmax = 0.989	k = −8→8
4974 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0852P)2 + 0.0886P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1629 reflections	Δρmax = 0.26 e Å−3
128 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (9)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.2834 (2)	0.1857 (2)	0.62203 (13)	0.0573 (4)
O2	−0.30931 (18)	0.3149 (2)	0.47149 (12)	0.0476 (4)
O3	−0.2182 (3)	0.2434 (3)	0.87960 (15)	0.0749 (5)
C1	0.2333 (3)	0.2150 (3)	0.34035 (18)	0.0415 (4)
H1A	0.3724	0.1795	0.3703	0.050*
C2	0.1952 (3)	0.2394 (3)	0.20506 (19)	0.0455 (5)
C3	−0.0162 (3)	0.2971 (3)	0.16259 (19)	0.0497 (5)
H3A	−0.0452	0.3169	0.0717	0.060*
C4	−0.1816 (3)	0.3252 (3)	0.25048 (19)	0.0494 (5)
H4A	−0.3210	0.3642	0.2199	0.059*
C5	−0.1371 (3)	0.2942 (3)	0.38609 (18)	0.0397 (4)
C6	−0.2734 (3)	0.2855 (3)	0.60304 (19)	0.0443 (5)
H6A	−0.3894	0.2953	0.6604	0.053*
C7	−0.0835 (3)	0.2431 (3)	0.65872 (18)	0.0396 (4)
C8	0.1067 (3)	0.2197 (3)	0.57661 (18)	0.0386 (4)
C9	0.0686 (3)	0.2422 (2)	0.43295 (17)	0.0360 (4)
C10	0.3734 (4)	0.2037 (4)	0.1063 (2)	0.0654 (6)
H10A	0.5069	0.1645	0.1524	0.098*
H10B	0.3537	0.3308	0.0316	0.098*
H10C	0.3733	0.0931	0.0717	0.098*
C11	−0.0697 (3)	0.2176 (3)	0.8057 (2)	0.0548 (5)
H11A	0.0649	0.1784	0.8440	0.066*

	U11	U22	U33	U12	U13	U23
O1	0.0400 (8)	0.0876 (10)	0.0504 (8)	−0.0238 (7)	−0.0042 (6)	−0.0252 (7)
O2	0.0330 (7)	0.0611 (8)	0.0441 (7)	−0.0130 (6)	−0.0026 (5)	−0.0121 (6)
O3	0.0733 (11)	0.1117 (13)	0.0537 (9)	−0.0380 (10)	0.0201 (8)	−0.0413 (9)
C1	0.0385 (9)	0.0444 (10)	0.0434 (10)	−0.0157 (8)	0.0003 (7)	−0.0138 (8)
C2	0.0522 (11)	0.0442 (10)	0.0401 (10)	−0.0176 (8)	0.0025 (8)	−0.0117 (8)
C3	0.0609 (12)	0.0530 (11)	0.0348 (9)	−0.0209 (9)	−0.0073 (8)	−0.0087 (8)
C4	0.0436 (10)	0.0553 (11)	0.0459 (11)	−0.0163 (9)	−0.0118 (8)	−0.0077 (8)
C5	0.0373 (9)	0.0369 (9)	0.0423 (10)	−0.0120 (7)	−0.0017 (7)	−0.0085 (7)
C6	0.0389 (10)	0.0465 (10)	0.0440 (10)	−0.0114 (8)	0.0043 (7)	−0.0133 (8)
C7	0.0419 (10)	0.0387 (9)	0.0403 (10)	−0.0145 (7)	0.0017 (8)	−0.0141 (7)
C8	0.0369 (9)	0.0385 (9)	0.0427 (9)	−0.0131 (7)	−0.0033 (7)	−0.0137 (7)
C9	0.0372 (9)	0.0325 (8)	0.0384 (9)	−0.0124 (7)	−0.0024 (7)	−0.0094 (7)
C10	0.0634 (14)	0.0885 (16)	0.0457 (11)	−0.0245 (12)	0.0091 (10)	−0.0256 (11)
C11	0.0550 (12)	0.0696 (13)	0.0482 (11)	−0.0241 (10)	0.0037 (9)	−0.0262 (10)

O1—C8	1.227 (2)	C4—H4A	0.9300
O2—C6	1.335 (2)	C5—C9	1.385 (2)
O2—C5	1.383 (2)	C6—C7	1.339 (3)
O3—C11	1.196 (2)	C6—H6A	0.9300
C1—C2	1.385 (3)	C7—C8	1.455 (2)
C1—C9	1.396 (2)	C7—C11	1.475 (3)
C1—H1A	0.9300	C8—C9	1.473 (2)
C2—C3	1.399 (3)	C10—H10A	0.9600
C2—C10	1.505 (3)	C10—H10B	0.9600
C3—C4	1.368 (3)	C10—H10C	0.9600
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.387 (3)
C6—O2—C5	117.99 (13)	C6—C7—C8	120.85 (16)
C2—C1—C9	121.75 (17)	C6—C7—C11	118.72 (16)
C2—C1—H1A	119.1	C8—C7—C11	120.43 (16)
C9—C1—H1A	119.1	O1—C8—C7	123.32 (16)
C1—C2—C3	117.68 (17)	O1—C8—C9	122.63 (16)
C1—C2—C10	121.76 (18)	C7—C8—C9	114.04 (15)
C3—C2—C10	120.56 (17)	C5—C9—C1	118.08 (16)
C4—C3—C2	122.15 (17)	C5—C9—C8	119.66 (16)
C4—C3—H3A	118.9	C1—C9—C8	122.26 (16)
C2—C3—H3A	118.9	C2—C10—H10A	109.5
C3—C4—C5	118.60 (17)	C2—C10—H10B	109.5
C3—C4—H4A	120.7	H10A—C10—H10B	109.5
C5—C4—H4A	120.7	C2—C10—H10C	109.5
O2—C5—C9	122.29 (16)	H10A—C10—H10C	109.5
O2—C5—C4	116.01 (15)	H10B—C10—H10C	109.5
C9—C5—C4	121.69 (16)	O3—C11—C7	125.06 (19)
O2—C6—C7	125.04 (16)	O3—C11—H11A	117.5
O2—C6—H6A	117.5	C7—C11—H11A	117.5
C7—C6—H6A	117.5
C9—C1—C2—C3	1.3 (3)	C6—C7—C8—C9	−1.3 (2)
C9—C1—C2—C10	−178.14 (16)	C11—C7—C8—C9	177.95 (15)
C1—C2—C3—C4	−1.3 (3)	O2—C5—C9—C1	176.96 (14)
C10—C2—C3—C4	178.17 (18)	C4—C5—C9—C1	−1.9 (3)
C2—C3—C4—C5	−0.3 (3)	O2—C5—C9—C8	−3.7 (3)
C6—O2—C5—C9	0.8 (2)	C4—C5—C9—C8	177.44 (15)
C6—O2—C5—C4	179.73 (15)	C2—C1—C9—C5	0.3 (3)
C3—C4—C5—O2	−176.99 (15)	C2—C1—C9—C8	−179.10 (15)
C3—C4—C5—C9	2.0 (3)	O1—C8—C9—C5	−175.79 (16)
C5—O2—C6—C7	2.0 (3)	C7—C8—C9—C5	3.7 (2)
O2—C6—C7—C8	−1.6 (3)	O1—C8—C9—C1	3.6 (3)
O2—C6—C7—C11	179.14 (16)	C7—C8—C9—C1	−176.89 (14)
C6—C7—C8—O1	178.25 (17)	C6—C7—C11—O3	−4.4 (3)
C11—C7—C8—O1	−2.5 (3)	C8—C7—C11—O3	176.35 (19)